Palladium-Catalyzed Cascade Reaction of o‑Cyanobiaryls with Arylboronic Acids: Synthesis of 5‑Arylidene-7-aryl‑5H‑dibenzo[c,e]azepines

A palladium-catalyzed cascade reaction of 2′-acetyl-[1,1′-biphenyl]-2-carbonitriles with arylboronic acids is developed. This reaction affords a new class of seven-membered 5-arylidene-7-aryl-5H-dibenzo­[c,e]­azepines with good functional group compatibility and selectivity. Reaction mechanistic stu...

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Bibliographic Details
Published in:Organic letters 2019-10, Vol.21 (19), p.7697-7701
Main Authors: Yao, Xinrong, Shao, Yinlin, Hu, Maolin, Xia, Yuanzhi, Cheng, Tianxing, Chen, Jiuxi
Format: Article
Language:English
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Summary:A palladium-catalyzed cascade reaction of 2′-acetyl-[1,1′-biphenyl]-2-carbonitriles with arylboronic acids is developed. This reaction affords a new class of seven-membered 5-arylidene-7-aryl-5H-dibenzo­[c,e]­azepines with good functional group compatibility and selectivity. Reaction mechanistic study suggests that this transformation involves carbopalladation of nitrile and subsequent intramolecular cyclization followed by oxidative Heck coupling.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02351